Ethanol → Ethyl 4,4,4-trifluoro-3-hydroxybutanoate

HRID 1614369Notes

Reaction equation

HRID 1614369 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:14])([F:13])[C:5](=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].C(O)C>C(Cl)Cl>[F:3][C:4]([F:13])([F:14])[CH:5]([OH:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 4311764Sodium borohydride

Product 1

HCID 136210Ethyl 4,4,4-trifluoro-3-hydroxybutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 91.2 g (2.4 mol) of sodium borohydride in 6 l of CH2Cl2 cooled at +2° C., are dropwise added 1473 g of ethyl 4,4,4-trifluoroacetoacetate while keeping temperature between +4° and +7° C. After the introduction, 100 ml of absolute ethanol are added while keeping temperature at +3° C. The reaction medium is washed with bicarbonated water. The organic phase is concentrated and the product is distilled at 78° C. under 10 mm Hg.

Workup

  1. temperaturecooled at +2° C.
  2. customtemperature between +4° and +7° C
  3. customat +3° C
  4. washThe reaction medium is washed with bicarbonated water
  5. concentrationThe organic phase is concentrated
  6. distillationthe product is distilled at 78° C. under 10 mm Hg

Sources & evidence

ORD record
ord-099ff42b91c14389a215d7b0bfff12fd
Source dataset
uspto-grants-1993_03
Patent number
US05196543

Reaction notes

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